(1S,2S,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol | 118013-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol
• 英文别名: 4a-carba-α-L-arabinofuranose；(1R,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
• CAS: 118013-55-1
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PHKHGSSZAJVEQK-FSIIMWSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1S,2S,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol 在 吡啶 作用下， 反应 15.0h， 生成 (1S,2S,3S,4R)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane
  参考文献：
  名称：

  Syntheses of (1S,2S,3S,4R)- and (1R,2R,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol, carbocyclic analogs of .alpha.-L-arabinofuranose and .beta.-D-ribofuranose

  摘要：

  DOI：

  10.1021/jo00263a005
• 作为产物：
  描述：

  (3R,4R)-3-(benzyloxy)-4-hydroxy-1-cyclopentene-1-methanol 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 (1S,2S,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol
  参考文献：
  名称：

  Syntheses of (1S,2S,3S,4R)- and (1R,2R,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol, carbocyclic analogs of .alpha.-L-arabinofuranose and .beta.-D-ribofuranose

  摘要：

  DOI：

  10.1021/jo00263a005

文献信息

• First synthesis of 4a-carba-β-d-galactofuranose
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.1016/j.tetlet.2007.10.138

  日期：2007.12

  The synthesis of 4a-carba-β-d-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the CC double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity.

  描述了从双丙酮葡萄糖开始的4a-氨基甲酸酯-β-d-半乳糖呋喃糖的合成。通过复分解进行关键环闭合步骤以形成环戊烯。CC双键的催化加氢得到具有出色的非对映选择性的半乳糖构型的饱和呋喃呋喃呋喃糖。
• Synthesis of All Stereoisomeric Carbapentofuranoses
  作者：Christoph Marschner、Judith Baumgartner、Herfried Griengl

  DOI：10.1021/jo00121a046

  日期：1995.8

  All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer-Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyre, and alpha-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3-position was found. If an epoxy acetate with both functions on the same side of the ring was used, the epoxide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.
• Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives
  作者：Jens Frigell、Lars Eriksson、Ian Cumpstey

  DOI：10.1016/j.carres.2011.04.032

  日期：2011.8

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.